A new type of functionalized discotic oligomer system has been realized whose molecular architecture consists of a trisubstituted benzene as central core and three nitro-functionalized triphenylenes as regional cores. These regional cores are linked to the central core via ether linkages through an alkyl chain spacer. Polarizing microscopy and calorimetric measurements reveal the existence of a monotropic columnar mesophase in this novel functionalized oligomer. The product does not crystallize at room temperature over a long period (c. five months) or on cooling to 50 C. The corresponding unfunctionalized trimer is not liquid crystalline. The dipolar interaction of nitro groups is probably responsible for the induction of mesogenicity. The introduction of functionality into liquid crystal oligomers permits the variation of their properties on a wide scale and opens the route to new synthetic supramolecular systems for various device applications.